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Chesapeake City vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chesapeake City

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Newark

4.99 out of 5 average rating, 166 reviews

Spacious, light filled studio 2 blocks from UDel

Our quiet, private studio is located in the historic Old Newark neighborhood, next to the Univ of Delaware, only a few minutes' walk to the center of downtown Newark. Newark is a thriving college town with restaurants, history museum, library, small stores erc. The studio is in a quiet, friendly, safe, historic and walkable neighborhood. If you are looking for privacy and serenity in this charming town, this is the place! Guests describe our studio as immaculately clean, private and calming.

Apr 21 – 28

R2,061 ZAR per night
Guest favorite

Guesthouse in Quarryville

4.99 out of 5 average rating, 222 reviews

The Olde Wash House on Camargo

Come and relax in our newly remodeled, cozy, cottage style home with it's own private entrance, surrounded by working Amish farms, just outside of town. A short 15 minute drive to Historic Strasburg, Sight and Sound Theater, Antique Shopping, Tangor Outlets and more! Hiking Trails close by include Enola Grade Trail, Pinnacle Point, Muddy Run Park, and Sickman's Mill. If golfing is your desire, Tanglewood Golf Club is just 10 minutes away. We hope you enjoy your stay!

Jan 6 – 13

R1,841 ZAR per night
Guest favorite

Apartment in Frederica

4.96 out of 5 average rating, 253 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

Dec 22 – 29

R1,419 ZAR per night

Popular amenities for Chesapeake City vacation rentals

Stay near Chesapeake City's top sights

Chesapeake Inn Restaurant & Marina41 locals recommend
Schaefer's Canal House33 locals recommend
Cafe on the Bay10 locals recommend
The Bayard House Restaurant16 locals recommend
Prime 22520 locals recommend
Tap Room Inc8 locals recommend

Other great vacation rentals in Chesapeake City

Guest favorite

Loft in Paradise

4.99 out of 5 average rating, 517 reviews

The Loft On Forever Lane

Nov 17 – 24

R1,881 ZAR per night
Guest favorite

Yurt in Elkton

5.0 out of 5 average rating, 103 reviews

Creekside Forest Nature Retreat : Mongolian Yurt

Nov 25 – Dec 2

R2,288 ZAR per night
Guest favorite

Guesthouse in Media

4.96 out of 5 average rating, 467 reviews

Studio Apartment in Attractive Sylvan Setting

Aug 11 – 18

R2,113 ZAR per night
Guest favorite

Apartment in New Castle

4.88 out of 5 average rating, 336 reviews

Blue Tranquility-Pvt Apt for Quiet Rest

Dec 16 – 23

R1,549 ZAR per night
Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 107 reviews

Scenic, private 2 room-guest suite, near Bel Air

Feb 2 – 9

R1,936 ZAR per night
Superhost

Guest suite in Bear

4.88 out of 5 average rating, 193 reviews

Luxurious apartment/studio with private entrance

Jan 16 – 23

R2,166 ZAR per night
Guest favorite

Apartment in Chesapeake City

4.95 out of 5 average rating, 63 reviews

hygge haven: hygge= happy + cozy

May 30 – Jun 6

R2,503 ZAR per night
Guest favorite

Cottage in Chesapeake City

5.0 out of 5 average rating, 52 reviews

Bohemia Bungalow

Feb 3 – 10

R4,340 ZAR per night
Guest favorite

Guest suite in Chesapeake City

5.0 out of 5 average rating, 75 reviews

Benson House on Bohemia Ave (Back Deck)

Apr 21 – 28

R3,417 ZAR per night
Guest favorite

Home in Chesapeake City

5.0 out of 5 average rating, 28 reviews

Charming, updated home in Historic Chesapeake City

Oct 8 – 15

R7,726 ZAR per night
Guest favorite

Apartment in Elkton

4.98 out of 5 average rating, 53 reviews

Short Term Water Oriented Furnished Apartment

Aug 28 – Sep 4

R2,520 ZAR per night
Guest favorite

Home in Chesapeake City

5.0 out of 5 average rating, 23 reviews

Wister Loft: Charm & History with Modern Love.

Jan 31 – Feb 7

R4,684 ZAR per night

Other great vacation rentals in Chesapeake City

Guest favorite

Home in Chesapeake City

5.0 out of 5 average rating, 79 reviews

Spring Season @ Old Lock View Chesapeake City MD

Jun 1 – 8

R7,785 ZAR per night
Guest favorite

Home in Chesapeake City

4.96 out of 5 average rating, 25 reviews

HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn

Dec 24 – 31

R15,975 ZAR per night
Guest favorite

Guesthouse in Elk Mills

4.97 out of 5 average rating, 37 reviews

Private Country Guesthouse Getaway Minutes from UD

Aug 5 – 12

R2,494 ZAR per night
Guest favorite

Home in Charlestown

4.91 out of 5 average rating, 66 reviews

Cozy cape cod in water oriented Community near I95

May 1 – 8

R2,563 ZAR per night
Guest favorite

Guesthouse in Elkton

4.93 out of 5 average rating, 73 reviews

Countryside~Stable House~Open Studio~Perfect for 2

Jul 23 – 30

R2,759 ZAR per night
Guest favorite

Cottage in Earleville

4.94 out of 5 average rating, 35 reviews

The Cottage at Crystal

Apr 27 – May 4

R2,956 ZAR per night
Guest favorite

Home in North East

4.94 out of 5 average rating, 90 reviews

Historic Creekside Home - 2br 2.5ba Downtown

Feb 5 – 12

R3,004 ZAR per night
Guest favorite

Farm stay in Lincoln University

4.96 out of 5 average rating, 55 reviews

Pyle Cottage circa 1750

Sep 23 – 30

R3,304 ZAR per night
Guest favorite

Home in Elkton

4.97 out of 5 average rating, 31 reviews

Waterfront Sunset River Cottage -perfect getaway

Oct 30 – Nov 6

R6,054 ZAR per night
Guest favorite

Home in Elkton

5.0 out of 5 average rating, 24 reviews

Elk River Cottage

Jun 12 – 19

R4,792 ZAR per night
Guest favorite

Guest suite in Newark

5.0 out of 5 average rating, 56 reviews

Inviting, comfortable & private suite near Univ.

Sep 10 – 17

R2,141 ZAR per night
Guest favorite

Cottage in Earleville

4.98 out of 5 average rating, 56 reviews

The Bohemia Charmer

Sep 10 – 17

R5,674 ZAR per night

Quick stats about vacation rentals in Chesapeake City

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.2K reviews

Nightly prices starting at

R1,894 ZAR before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Cecil County
  5. Chesapeake City